Diisopropylethylamine → 3-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796034노트

반응식

HRID 1796034 반응식
FC(F)(F)S([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])(=O)=O.[Br:16][C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26](O)([CH3:28])[CH3:27])=[N:25][C:20]2=[N:19][CH:18]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Br:16][C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26]([CH3:28])([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])[CH3:27])=[N:25][C:20]2=[N:19][CH:18]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol

생성물 1

HCID 695598483-Bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Triethylsilyl trifluoromethanesulfonate (4.85 ml, 21.5 mmol) was added dropwise over 15 min to a cooled (−50° C.) solution of 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (5.0 g, 19.5 mmol) and diisopropylethylamine (4.76 ml, 27.5 mmol) in dichloromethane (150 ml). The mixture was stirred for 20 min then allowed to warm to ambient temperature overnight. The reaction mixture was diluted with dichloromethane (100 ml) and washed with 1N hydrochloric acid (100 ml) and water (100 ml), dried over anhydrous magnesium sulfate, filtered and evaporated. The red oil was purified by dry flash column chromatography on silica eluting with dichloromethane on a gradient of methanol (0-3%). Collecting the appropriate fractions gave 3-bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine as a pale yellow oil which crystallised on standing (6.21 g, 86%): δH (400 MHz, CDCl3) 0.64 (6H, q, J 8), 0.97 (9H, t, J 8), 7.50 (1H, d, J 7), 7.72 (1H, s), 8.35 (1H, d, J 7).

후처리

  1. washwashed with 1N hydrochloric acid (100 ml) and water (100 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe red oil was purified
  6. dry with materialby dry flash column chromatography on silica eluting with dichloromethane on a gradient of methanol (0-3%)
  7. customCollecting the appropriate fractions

출처 및 근거

ORD 기록
ord-9500595a69d14aa489c407fa205b6bf5
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030128B2

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